Dioxyphenyl-alpha-propanolamin.



UNITED STATES PATENT OFFICE. WILHELM GEt'I'r'rEEIEN, or VlDHWINKEL, NEAR ELBERFELD, GERMANY, ASSIGNOR r0 FARBENFABRIKEN vonm. FRIEDR. BAYER & 00., 0E ELBERFELD, GERMANY, A

CORPORATION OF GERMANY.

DIOXYPHENYL-ALPHA-PROPANOLAMI1\T.

No Drawing.

Specification of Letters Patent.

Application filed April 26, 1912. Serial No. 693,452.

Patented Nov. 19, 1912.

by means of metals of the platinum group and hydrogen. 1

The racemic product thus obtained can be resolved into the two optically active bases by means of the dextroand levo-tartaric acid The new products have the valuable therapeutic property of increasing the bloodpressure in the same way as the substance contained in the suprarenal glands.

In order to illustrate the new process more fully the following example is given, the parts being by weight :5 parts of palladious chlorid and 10 parts of gum arabic are dissolved in 300 parts of hot water together with a small quantity of dilute hydrochloric acid. The resulting solution is reduced with hydrazin hydrate, 100 parts of the hydrochlorid of alpha-aminopropionyl-pyrocatechin (M. P. 236 C.) are added thereto and the mixture is brought into a pressure flask. Into this flask at a temperature of about 20 C. and under a pressure of 1 atmosphere hydrogen is introduced during 23 days until the reduction is complete.

Subsequently 300 parts of acetone are added,

the liquid is filtered and the filtrate is evaporated at C. in cacao. The residue is dissolved in water and the product is precipitated with 20 per cent. ammonia solution, filtered off, washed with alcohol, ether and acetone and dried. It melts at 204 C. The hydrochlorid (free from crystal alcohol) melts at 17 7 C. It is soluble in water giving with FeCl a deep green coloration. The product thus obtained can be resolved into the active compounds by means of levoor dextro-tartaric acid. The dextro-base is a white powder melting at 217 C. It is deXt-ro-rotatory The levo-base melts at 218 C. It is levorotatory oaD=-30.00.

I-claim:-- 1. The new dioxy-phenyl-alpha-propanolamin melting at 204 (3., in the form of its hydrochlorid melting at 177 C., which can be resolved into optically active compounds, the dextro-base melting at 217 C., the levobase at 218 (3., all possessing valuable properties, substantially as described.

2. The new dioxy-phenyl-alpha-propanolamins which are optically active bases possessing valuable therapeutical properties substantially as described.

In testimony whereof I have hereunto set' my hand in the presence of two subscribing witnesses.

WILHELM GRUTTEFIEN. [L.s.] Witnesses:

HELEN N UEE ALBERT NUFER. 

